Substituted aryl ketones

ABSTRACT

The invention relates to novel substituted aryl ketones of the general formula (I)  
                 
 
     in which  
     n represents the number 0, 1 or 2,  
     A represents alkanediyl (alkylene),  
     R 1  represents one of the groupings below  
                 
 
     where  
     m, R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12  and R 13  each have one of the meanings given in the description,  
     R 2  represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,  
     R 3  represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and  
     R 4  represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic heterocyclic grouping,  
     and to processes for their preparation, to intermediates and to the use of these compounds as herbicides.

[0001] The invention relates to novel substituted aryl ketones, toprocesses for their preparation and to their use as herbicides.

[0002] It is already known that certain substituted aryl ketones haveherbicidal properties (cf. EP-A-090262, EP-A-135191, EP-A-186118,EP-A-186119, EP-A-186120, EP-A-319075, EP-A-352543, EP-A-418175,EP-A-487357, EP-A-527036, EP-A-527037, EP-A-560483, EP-A-609797,EP-A-609798, EP-A-625505, EP-A-625508, EP-A-636622, U.S. Pat. No.5,804,532, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,846,906, U.S. Pat.No. 5,863,865, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200,WO-A-96/26206, WO-A-97/27187, WO-A-97/35850, WO-A-97/41105,WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270,WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-98/31682,WO-A-99/03856, WO-A-99/07688, WO-A-99/10327, WO-A-99/10328). However,the activity of these compounds is not entirely satisfactory.

[0003] This invention, accordingly, provides the novel substituted arylketones of the general formula (I)

[0004] in which

[0005] n represents the number 0, 1 or 2,

[0006] A represents alkanediyl (alkylene),

[0007] R¹ represents one of the groupings below

[0008] where

[0009] m represents the numbers 0 to 6,

[0010] R⁵ represents halogen or represents in each case optionallysubstituted alkyl, alkylthio or aryl or—if m represents 2—optionallyalso together with a second radical R⁵ represents alkanediyl (alkylene),

[0011] R⁶ represents hydroxyl, formyloxy, halogen, or represents in eachcase optionally substituted alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio,arylalkylsulphinyl or arylalkylsulphonyl,

[0012] R⁷ represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl or cycloalkyl,

[0013] R⁸ represents hydrogen or represents in each case optionallysubstituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylor arylalkyl,

[0014] R⁹ represents hydroxyl, formyloxy, or represents in each caseoptionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy,

[0015] R¹⁰ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl oralkylsulphonyl,

[0016] R¹¹ represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl,

[0017] R¹² represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl, and

[0018] R¹³ represents hydrogen, cyano, carbamoyl, halogen, or representsin each case optionally substituted alkyl, alkoxy, alkoxycarbonyl,alkylthio, alkylsulphinyl or alkylsulphonyl,

[0019] R² represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl,

[0020] R³ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,dialkylamino or dialkylaminosulphonyl, and

[0021] R⁴ represents an optionally substituted 4- to 12-membered,saturated or unsaturated, monocyclic or bicyclic heterocyclic groupingwhich contains 1 to 4 hetero atoms (up to 4 nitrogen atoms andoptionally—alternatively, or additionally—one or two oxygen atoms or oneor two sulphur atoms, or one or two SO groupings or one or two SO₂groupings), and which additionally contains one to three oxo groups(C═O) and/or thioxo groups (C═S) as components of the heterocycle,

[0022] including all possible tautomeric forms of the compounds of thegeneral formula (I) and the possible salts and acid or base adducts ofthe compounds of the general formula (I)—.

[0023] In the definitions, the hydrocarbon chains, such as alkyl oralkanediyl, are in each case straight-chain or branched - including incombination with heteroatoms, such as in alkoxy.

[0024] The compounds of the general formula (I) according to theinvention may contain one or more asymmetrically substituted carbonatoms, and they may therefore be present in different enantiomeric (R-and S-configured forms) or diastereomeric forms. The invention relatesboth to the various possible individual enantiomeric or stereoisomericforms of the compounds of the general formula (I) and to the mixtures ofthese stereoisomeric compounds.

[0025] Preferred substituents or preferred ranges of the radicalspresent in the formulae listed above and below are defined below.

[0026] n preferably represents the number 0 or 1.

[0027] m preferably represents the number 0, 1, 2, 3 or 4.

[0028] A preferably represents alkanediyl (alkylene) having 1 to 6carbon atoms.

[0029] R¹ preferably represents one of the groupings below

[0030] R² preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups.

[0031] R³ preferably represents nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano,halogen, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups.

[0032] R⁴ preferably represents one of the heterocyclic groupings below

[0033] where in each case the broken bond is a single bond or a doublebond.

[0034] Q represents oxygen or sulphur,

[0035] R¹⁴ represents hydrogen, hydroxyl, mercapto, cyano, halogen,represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms in the alkyl groups, represents in eachcase optionally halogen-substituted alkylamino or dialkylamino having ineach case up to 6 carbon atoms in the alkyl groups, represents in eachcase optionally halogen-substituted alkenyl, alkinyl, alkenyloxy,alkenylthio or alkenylamino having in each case up to 6 carbon atoms inthe alkenyl or alkinyl groups, represents in each case optionallyhalogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio,cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthioor cycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally up to 4 carbon atoms in the alkylmoiety, or represents in each case optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino,piperidino or morpholino, or—if two adjacent radicals R¹⁴ and R¹⁴ arelocated at a double bond—also together with the adjacent radical R¹⁴represents a benzo grouping, and

[0036] R¹⁵ represents hydrogen, hydroxyl, amino, alkylideneamino havingup to 4 carbon atoms, represents in each case optionally halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino oralkanoylamino having in each case up to 6 carbon atoms in the alkylgroups, represents in each case optionally halogen-substituted alkenyl,alkinyl or alkenyloxy having in each case up to 6 carbon atoms in thealkenyl or alkinyl groups, represents in each case optionallyhalogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylaminohaving in each case 3 to 6 carbon atoms in the cycloalkyl groups andoptionally up to 3 carbon atoms in the alkyl moiety, or represents ineach case optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedphenyl or benzyl, or together with an adjacent radical R¹⁴ or R¹⁵represents optionally halogen- or C₁-C₄-alkyl-substituted alkanediylhaving 3 to 5 carbon atoms,

[0037] where the individual radicals R¹⁴ and R¹⁵—if more than one ofthem are attached to the same heterocyclic groupings—can have identicalor different meanings within the scope of the above definition.

[0038] R⁵ preferably represents halogen, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl oralkylthio having in each case 1 to 6 carbon atoms, represents optionallyhalogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl, or optionallyalso—if m represents 2—together with a second radical R⁵ representsalkanediyl (alkylene) having 2 to 6 carbon atoms.

[0039] R⁶ preferably represents hydroxyl, formyloxy, or represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy-substitutedalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy,alkoxycarbonyloxy-, alkylaminocarbonyloxy or alkylsulphonyloxy having ineach case 1 to 6 carbon atoms in the alkyl groups, represents in eachcase optionally cyano- or halogen-substituted alkenyloxy or alkinyloxyhaving in each case 2 to 6 carbon atoms, or represents in each caseoptionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted aryloxy, arylthio,arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy,arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl orarylalkylsulphonyl having in each case 6 or 10 carbon atoms in the arylgroup and optionally 1 to 4 carbon atoms in the alkyl moiety.

[0040] R⁷ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1to 6 carbon atoms in the alkyl groups, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms.

[0041] R⁸ preferably represents hydrogen, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1to 6 carbon atoms, represents in each case optionally cyano- orhalogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in eachcase 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4carbon atoms in the alkyl moiety, or represents in each case optionallynitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted aryl or arylalkylhaving in each case 6 or 10 carbon atoms in the aryl group andoptionally 1 to 4 carbon atoms in the alkyl moiety.

[0042] R⁹ preferably represents hydroxyl, formyloxy, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkoxy,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, orrepresents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogeno-alkoxy-substituted arylalkoxy, arylcarbonyloxy,arylcarbonylalkoxy or arylsulphonyloxy having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety.

[0043] R¹⁰ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 6 carbon atoms in the alkyl groups.

[0044] R¹¹ preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms orrepresents optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl having 3 to 6 carbon atoms.

[0045] R¹² preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms orrepresents optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl having 3 to 6 carbon atoms.

[0046] R¹³ preferably represents hydrogen, cyano, carbamoyl, halogen, orrepresents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl groups.

[0047] m particularly preferably represents the numbers 0, 1, 2 or 3.

[0048] A particularly preferably represents methylene, ethane-1,2-diyl(dimethylene), ethane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl(trimethylene), butane-1,2-diyl, butane-1,3-diyl or butane-1,4-diyl(tetramethylene).

[0049] R² particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine-, bromine,iodine, or represents in each case optionally fluorine- and/orchlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine- and/orchlorine-, methoxy-ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy,n- or i-propoxy, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or representsmethylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.

[0050] R³ particularly preferably represents nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents ineach case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine- and/or chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, represents in each case fluorine- and/or chorine-substitutedmethylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl

[0051] R⁴ particularly preferably represents one of the heterocyclicgroupings below.

[0052] R⁵ particularly preferably represents fluorine, chlorine,bromine, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-,i-, s- or t-butylthio, represents optionally fluorine-, chlorine-,methyl- or methoxy-substituted phenyl, or optionally also - if mrepresents 2—together with a second radical R⁵ representsethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) orbutane-1,4-diyl (tetramethylene).

[0053] R⁶ particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-,s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, benzoyloxy,benzoylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio,phenylmethylsulphinyl or phenylmethylsulphonyl.

[0054] R⁷ particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0055] R⁸ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-,s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenyl or benzyl.

[0056] R⁹ particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy,represents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, propoxy-, n-, i-,s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenylmethoxy, benzoyloxy, benzoylmethoxy or phenylsulphonyloxy.

[0057] R¹⁰ particularly preferably represents hydrogen, cyano,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-,ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl.

[0058] R¹¹ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0059] R¹² particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0060] R¹³ particularly preferably represents hydrogen, cyano,carbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.

[0061] R¹⁴ particularly preferably represents hydrogen, hydroxyl,mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in eachcase optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- ori-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-,ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-,i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, represents methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,di-n-propylamino or di-i-propylamino, represents in each case optionallyfluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl,ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio,butenylthio, propenylamino or butenylamino, represents in each caseoptionally fluorine- and/or chlorine-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-,n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substitutedphenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy,benzylthio or benzylamino, represents pyrrolidino, piperidino ormorpholino, or—if two adjacent radicals R¹⁴ and R¹⁴ are located at adouble bond—together with the adjacent radical R¹⁴ also represents abenzo grouping.

[0062] R¹⁵ particularly preferably represents hydrogen, hydroxyl, amino,represents in each case optionally fluorine- and/or chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i- or s-butyl, methoxy,ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino,represents in each case optionally fluorine- and/or chlorine-substitutedethenyl, propenyl, ethinyl, propinyl or propenyloxy, represents in eachcase optionally fluorine- and/or chlorine-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, or represents ineach case optionally fluorine-, chlorine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- ori-propoxy-substituted phenyl or benzyl, or together with an adjacentradical R¹⁴ or R¹⁵ represents in each case optionally methyl- and/orethyl-substituted propane-1,3-diyl (trimethylene) or butane-1,4-diyl(tetramethylene).

[0063] A very particularly preferably represents methylene ordimethylene.

[0064] m very particularly preferably represents the number 0, 1 or 2,

[0065] R² very particularly preferably represents hydrogen, nitro,cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl,difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl,methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0066] R³ very particularly preferably represents nitro, cyano,fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0067] R⁵ very particularly preferably represents in each caseoptionally fluorine- or chlorine-substituted methyl, ethyl, n- ori-propyl, methylthio, ethylthio, n- or i-propylthio, represents phenyl,or optionally also—if m represents 2—together with a second radical R⁵represents ethane-1,2-diyl (dimethylene), propane-1,3-diyl(trimethylene) or butane-1,4-diyl (tetramethylene).

[0068] R⁶ very particularly preferably represents hydroxyl, formyloxy,represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n- ori-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n-or i-propylsulphonyloxy, represents propenyloxy or propinyloxy, orrepresents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-,ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenoxy, phenylthio, phenylsulphinyl,phenylsulphonyl, benzoyloxy, benzoylmethoxy, phenylsulphonyloxy,phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl orphenylmethylsulphonyl.

[0069] R⁷ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl.

[0070] R⁸ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted propenyl or propinyl,represents optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, or represents in each case optionallyfluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl or benzyl.

[0071] R⁹ very particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents propenyloxy or propinyloxy, orrepresents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-,ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenylmethoxy, benzoyloxy, benzoylmethoxyor phenylsulphonyloxy.

[0072] R¹⁰ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substitutedmethyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl,methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.

[0073] R¹¹ very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl.

[0074] R¹² very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl.

[0075] R¹³ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl.

[0076] R¹⁴ very particularly preferably represents hydrogen, hydroxyl,mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in eachcase optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substitutedmethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino,ethylamino, n- or i-propylamino, dimethylamino or diethylamino,represents in each case optionally fluorine- and/or chlorine-substitutedethenyl, propenyl, ethinyl, propinyl, propenyloxy, propenylthio orpropenylamino, represents in each case optionally fluorine- and/orchlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropylamino,cyclopropylmethyl, cyclopropylmethoxy or cyclopropylmethylamino, orrepresents in each case optionally fluorine-, chlorine-, methyl-,ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-substitutedphenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy,benzylthio or benzylamino, or—if two adjacent radicals R¹⁴ and R¹⁴ arelocated at a double bond—together with the adjacent radical R¹⁴ alsorepresents a benzo grouping.

[0077] R¹⁵ very particularly preferably represents hydrogen, hydroxyl,amino, represents in each case optionally fluorine- and/or chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino,represents propenyl or propinyl, represents in each case optionallyfluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl orcyclopropylmethyl, or represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- ori-propoxy-substituted phenyl or benzyl, or together with an adjacentradical R¹⁴ or R¹⁵ represents in each case optionally methyl- and/orethyl-substituted propane-1,3-diyl (trimethylene) or butane-1,4-diyl(tetramethylene).

[0078] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred.

[0079] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0080] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0081] Particular emphasis is given to the compounds of the generalformulae (I-1) to (I-3):

[0082] Here, n, A, R¹, R², R³ and R⁴ in each case have the mostpreferred meaning. Very particular emphasis is given to the compounds ofthe general formulae (I-2A) to (I-2D):

[0083] Here, m, n, A, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² andR¹³ in each case have the most preferred meaning.

[0084] The invention also provides the sodium, potassium, magnesium,calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-sulphonium, C₅— or C₆-cycloalkyl-ammonium anddi-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I)in which preferably n, A, R¹, R², R³ and R⁴ have the meanings givenabove as being preferred, particularly preferred or very particularlypreferred.

[0085] The general or preferred radical definitions given above applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

[0086] The novel substituted aryl ketones of the general formula (I)have strong and selective herbicidal activity.

[0087] the novel substituted aryl ketones of the general formula (I) areobtained when

[0088] (a) substituted benzoic acids of the general formula (ii)

[0089] in which

[0090] n, A, R², R³ and R⁴ are each as defined above,

[0091] or reactive derivatives thereof, such as, for example, thecorresponding acid halides, acid cyanides or esters—

[0092] are reacted with compounds of the general formula (m)

R¹—H  (III)

[0093] in which

[0094] R¹ is as defined above,

[0095] if appropriate in the presence of a dehydrating agent, ifappropriate in the presence of one or more reaction auxiliaries and ifappropriate in the presence of a diluent,

[0096] or where

[0097] (b) substituted benzoyl ketones of the general formula (Ia)

[0098] in which

[0099] n, A, R², R³, R⁴ and R¹¹ are each as defined above,

[0100] are reacted with an orthoformic ester or a N,N-dimethyl-formamideacetal or with a cyanoformic ester or with carbon disulphide and analkylating agent, and then with hydroxylamine or an acid adduct thereof,

[0101] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0102] and, if appropriate, following the practice of the process (a) or(b) according to the invention, the resulting compounds of the generalformula (I) are subjected in a customary manner to substitution,oxidation or reduction reactions within the scope of the definition ofthe substituents and/or the compounds of the general formula (I) areconverted in a customary manner into salt-like compounds.

[0103] Using, for example, 4-chloro-3-[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-methoxy]-2-fluoro-benzoic acid and1,3-dimethyl-5-hydroxy-pyrazole as starting materials, the course of thereaction in the process (a) according to the invention can beillustrated by the following equation:

[0104] Using, for example,1-[2-chloro-4-methyl-3-[2-(2-oxo-1(2H)-pyridinyl)-ethoxy]-phenyl]-3-cyclopropyl-1,3-propanedione,ethyl cyanoformate and hydroxylamine as starting materials, the courseof the reaction in the process (b) according to the invention can beillustrated by the following equation:

[0105] The formula (II) provides a general definition of the substitutedbenzoic acids to be used as starting materials in the process (a)according to the invention for preparing compounds of the generalformula (I). In the general formula (II), n, A, R², R³ and R⁴ eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for n, A, R², R³ and R⁴.

[0106] The starting materials of the general formula (II) have hithertonot been disclosed in the literature; as novel substances, they alsoform part of the subject-matter of the present application.

[0107] The novel substituted benzoic acids—or else their derivatives,such as their esters, in particular the methyl esters and ethylesters—are obtained when

[0108] (α) Compounds of the Formula (IV)

[0109] in which

[0110] n, A, R² and R³ are each as defined above and

[0111] X¹ represents halogen (in particular fluorine, chlorine orbromine) or represents alkylsulphonyloxy (in particularmethylsulphonyloxy or ethylsulphonyloxy),

[0112] or else their derivatives, such as their esters, in particularthe methyl esters and ethyl esters—

[0113] are reacted with heterocyclic compounds of the general formula(V)

H—R⁴  (V)

[0114] in which

[0115] R⁴ is as defined above,

[0116] if appropriate in the presence of an acid acceptor, such as, forexample, potassium carbonate, and if appropriate in the presence of adiluent, such as, for example, acetone, butanone, acetonitrile,N,N-dimethyl-formamide or dimethyl sulphoxide, at temperatures between10° C. and 150° C., followed, if appropriate, by further customaryconversion reactions within the scope of the definition of thesubstituents (cf. the Preparation Examples),

[0117] or when

[0118] (β) Compounds of the Formula (VI)

[0119] in which

[0120] n, R² and R³ are each as defined above

[0121] or else their derivatives, such as their esters, in particularthe methyl esters and ethyl esters—

[0122] are reacted with hydroxyalkylheterocycles of the general formula(VII)

[0123] in which

[0124] A and R⁴ are each as defined above,

[0125] in the presence of condensing auxiliaries, such as, for example,diethyl azodicarboxylate and triphenylphosphine, if appropriate in thepresence of a diluent, such as, for example, tetrahydrofuran attemperatures between −20° C. and +50° C., followed, if appropriate, byfurther customary conversion reactions within the scope of thedefinition of the substituents (cf. the Preparation Examples),

[0126] or when

[0127] (γ) Compounds of the Formula (VI)

[0128] in which

[0129] n, R² and R³ are each as defined above,

[0130] or else their derivatives, such as their esters, in particularthe methyl esters and ethyl esters—

[0131] are reacted with halogenoalkylheterocycles of the general formula(VIII)

[0132] in which

[0133] A and R⁴ are each as defined above and

[0134] X² represents halogen (in particular fluorine, chlorine orbromine), represents alkylsulphonyloxy (in particular methylsulphonyloxyor ethylsulphonyloxy), or represents arylsulphonyloxy (in particularp-tolylsulphonyloxy),

[0135] if appropriate in the presence of an acid acceptor, such as, forexample, potassium carbonate or triethylamine, and if appropriate in thepresence of a diluent, such as, for example, acetone, butanone,acetonitrile, N,N-dimethyl-formamide or dimethyl sulphoxide, attemperatures between 0° C. and 150° C., followed, if appropriate, byfurther customary conversion reactions within the scope of thedefinition of the substituents (cf. the Preparation Examples).

[0136] The formula (III) provides a general definition of the compoundsfurther to be used as starting materials in the process (a) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (III), R¹ preferably has that meaning which has alreadybeen mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor R¹.

[0137] The starting materials of the general formula (III) are knownorganic compounds.

[0138] The formula (Ia) provides a general definition of the substitutedbenzoyl ketones to be used as starting materials in the process (b)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), n, A, R², R³, R⁴ and R¹¹ eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for n, A², R³, R⁴ and R¹¹.

[0139] The starting materials of the general formula (Ia) are novelcompounds according to the invention; they can be prepared by theprocess (a) according to the invention.

[0140] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using a dehydrating agent. Suitable dehydratingagents are the customary chemicals suitable for binding water.

[0141] Examples of these which may be mentioned aredicyclohexylcarbodiimide and carbonyldllmidazole.

[0142] A particularly suitable dehydrating agent which may be mentionedis dicyclohexylcarbodiimide.

[0143] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using one or more reaction auxiliaries.

[0144] Examples of these which may be mentioned are sodium cyanide,potassium cyanide, acetone cyanohydrin,2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilyl cyanide.

[0145] The particularly suitable further reaction auxiliary which may bementioned is trimethylsilyl cyanide.

[0146] The process (a) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using a further reaction auxiliary. Suitablefurther reaction auxiliaries for the process according to the inventionare, in general, basic organic nitrogen compounds, such as, for example,trimethylamine, triethylamine, tripropylamine, tributylamine,ethyl-diiso-propylamine, N,N-dimethyl-cyclohexylamine,dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine,N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

[0147] The process (b) according to the invention for preparing thecompounds of the formula (I) is, if appropriate, carried out usingorthoformic esters or N,N-dimethylformamide acetals. These compoundspreferably contain alkyl groups having 1 to 4 carbon atoms, inparticular methyl or ethyl. Examples which may be mentioned aretrimethyl orthoformate, triethyl orthoformate, N,N-dimethyl-formamidedimethyl acetal and N,N-dimethyl-formamide diethylacetal.

[0148] The process (b) according to the invention for preparingcompounds of the formula (I) is, if appropriate, carried out usingcyanoformic esters. These compounds preferably contain alkyl groupshaving 1 to 4 carbon atoms, in particular methyl or ethyl. The exampleswhich may be mentioned are methyl cyanoformate and ethyl cyanoformate.

[0149] The process (b) according to the invention for preparingcompounds of the formula (I) is, if appropriate, carried out using(carbon disulphide and) alkylating agents. These compounds preferablycontain alkyl groups having 1 to 4 carbon atoms, in particular methyl orethyl. Examples which may be mentioned are methyl chloride, methylbromide, methyl iodide, dimethyl sulphate, ethyl chloride, ethylbromide, ethyl iodide and diethyl sulphate.

[0150] The process (b) according to the invention for preparingcompounds of the formula (I) is carried using hydroxylamine or an acidadduct thereof. Hydroxylamine hydrochloride may be mentioned aspreferred acid adduct.

[0151] The processes according to the invention for preparing thecompounds of the general formula (I) are preferably carried out usingdiluents. Suitable diluents for carrying out the processes (a) and (b)according to the invention are especially inert organic solvents. Theseinclude, in particular, aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as, for example, benzine, benzene,toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride;ethers, such as diethylether, diisopropylether, dioxane, tetrahydrofuranor ethylene glycol dimethyl ether or ethylene glycol diethyl ether;ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles,such as acetonitrile, propionitrile or butyronitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide,N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate; sulphoxides, such asdimethylsulphoxide; alcohols, such as methanol, ethanol, n- ori-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethylether, diethylene glycol monomethyl ether, diethylene glycol monoethylether.

[0152] When carrying out the processes (a) and (b) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

[0153] The processes (a) and (b) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to carry out the processes according to the invention underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

[0154] For carrying out the processes (a) and (b) according to theinvention, the starting materials are generally employed inapproximately equimolar amounts. However, it is also possible to use arelatively large excess of one of the components. The reaction isgenerally carried out in a suitable diluent and the reaction mixture isgenerally stirred at the required temperature for several hours. Work-upis carried out by customary methods (cf. the Preparation Examples).

[0155] The compounds of the formulae (IV), (V), (VI), (VII) and (VIII)to be used as starting materials in the process according to theinvention for preparing compounds of the general formula (II) are knownorganic compounds.

[0156] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0157] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0158] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0159] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0160] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0161] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0162] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0163] The active compounds accordingly to the invention are suitable,depending On the concentration, for the total control of weeds, forexample on industrial terrain and rail tracks, and on paths and areaswith and without tree plantings. Similarly, the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0164] The compounds of the formula (I) according to the invention havestrong herbicidal activity and a broad active spectrum when used on thesoil and on above-ground parts of plants. To a certain extent they arealso suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledononscrops, bothby the pre-emergence and by the post-emergence method.

[0165] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacterial plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0166] According to the invention, it is possible to treat all plantsand parts of plants. Plants are to be understood here as meaning allplants and plant populations such as desired and undesired wild plantsor crop plants (including naturally occurring crop plants). Crop plantscan be plants which can be obtained by conventional breeding andoptimization methods or by biotechnological and genetic engineeringmethods or combinations of these methods, including the transgenicplants and including plant cultivars which can or cannot be protected byplant breeders certificates. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, trunks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

[0167] The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or rage area according to customarytreatment methods, for exaiiipl by dippiny, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

[0168] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic substancesimpregnated with active compound, and microencapsulations in polymericsubstances.

[0169] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, optionally with the use of surfactants,that is to say emulsifiers and/or dispersants and/or foam-formers.

[0170] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Liquid solvents whichare mainly suitable are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and water.

[0171] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors arIu methylcellulose.

[0172] Tackifiers, such as carboxyl methylcellulose, natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0173] It is possible to use colorants, such as inorganic pigments, forexample iron oxide, titanium oxide, Prussian blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients, such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0174] The formulations generally comprise between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0175] For controlling weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0176] Possible components for the mixtures are known herbicides, forexample acetochlor, acifluorfen (-sodium), aclonifen, alachlor,alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulphuron,anilofos, asulam, atrazine, azafenidin, azimsulphuron, BAS-662H,beflubutamid, benazolin (-ethyl), benfuresate, bensulphuron (-methyl),bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide,bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim,butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulphuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulphuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulphuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulphamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (—P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, difiufenican,difiufenzopyr, dimefuron, dimepiperate, dimethachior, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulphuron (-methyl), ethofumesate, ethoxyfen, ethoxysulphuron,etobenzanid, fenoxaprop (—P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulphuron, florasulam, fluazifop(—P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam,flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam,fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam,flupropacil, flurpyrsulphuron (-methyl, -sodium), flurenol (-butyl),fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen,foramsulphuron, glufosinate (-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, —P-methyl),hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic,imazapyr, imazaquin, imazethapyr, imazosulphuron, iodosulphuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, mecoprop, mefenacet, mesosulphuron, mesotrione,metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron,(alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulphuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon,nicosulphuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon,oxasulphuron, oxaziclomefone, oxyfluorfen, paraquat, pelargon acid,pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen,piperophos, pretilachlor, primisulphuron (-methyl), profluazol,prometryn, propachlor, propanil, propaquizafop, propisochlor,procarbazone (-sodium), propyzamide, prosulphocarb, prosulphuron,pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulphuron (-ethyl),pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (—P-ethyl, —P-tefuryl),rimsulphuron, sethoxydim, simazine, simetryn, sulcotrione,sulphentrazone, sulphometuron (-methyl), sulphosate, sulphosulphuron,tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn,thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulphuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate,triasulphuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulphuron, triflusulphuron (-methyl), trito-sulphuron.

[0177] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0178] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0179] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0180] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0181] The preparation and the use of the active compounds according tothe invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

[0182]

[0183] (Process (a))

[0184] 0.30 g of (2.7 mmol) of 1-ethyl-5-hydroxy-pyrazole, 0.8 g (8.0mmol) of triethylamine and a drop of N,N-dimethyl-formamide are addedsuccessively to a solution of 1.1 g (2.7 mmol) of3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-4-methylsulphonyl-benzoylchloride in 20 ml of dichloromethane. The mixture is stirred at roomtemperature (about 20° C.), for about 24 hours, the reaction solution iswashed successively with 1N hydrochloric acid and saturated sodiumchloride solution and dried over magnesium sulphate and the solvent isremoved under water pump vacuum. The residue is dissolved in 30 ml ofacetonitrile and, with slight cooling, admixed successively with 0.28 g(3.3 mmol) of 2-hydroxyl-2-methylpropionitrile and 1.4 g (14 mmol) oftriethylamine. The mixture is stirred at room temperature for another 24hours, the major part of the solvent is removed under water pump vacuumand the residue is dissolved in dichloromethane and 1N hydrochloricacid. The organic phase is separated off, washed with water andsaturated sodium chloride solution, dried over magnesium sulphate andfiltered. From the filtrate, the solvent is carefully distilled offunder reduced pressure.

[0185] This gives 1.1 g (88% of theory) of4-{3-[2-(3′,4‘-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethyloxy]-2-methyl-4-methylsulphonyl-benzoyl}-1-ethyl-5-hydroxy-1H-pyrazoleas an oily residue.

[0186] Log P: 1.23.

Example 2

[0187]

[0188] (Process (a))

[0189] 1.95 g (5,4 mmol) of3-(3′-ethoxy-4′-methyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-methoxy-2,4-dichloro-benzoicacid are dissolved in 75 ml of acetonitrile and mixed with 0.61 g of1,3-cyclohexanedione (5.4 mmol) and 1.33 g of dicyclohexylcarbodiimide(DCC, 1.2 equivalents). The mixture is stirred at room temperature(about 20° C.) for 15 hours, and 1.5 ml of triethylamine (2 equivalents)and 0.29 ml of trimethylsilyl cyanide (0.4 equivalents) are then added.After 2 hours at room temperature, the mixture is concentrated underwater pump vacuum and the residue is stirred with 10% strength aqueoussodium carbonate solution and filtered off. The filtrate is shaken withdiethylether and the aqueous phase is acidified with 2N hydrochloricacid. The precipitated product is extracted repeatedly withdichloromethane and the combined organic phases are dried over sodiumsulphate, filtered and concentrated.

[0190] This gives 1.3 g (53% of theory) of2-[3-(3′-ethoxy-4′-methyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-methoxy-2,4-dichloro-benzoyl]-1,3-cyclohexanedioneas a viscous resin.

[0191] LogP=2.52.

[0192] Analogously to Examples 1 and 2, and in accordance with thegeneral description of the preparation processes according to theinvention, it is also possible to prepare, for example, the compounds ofthe general formula (I) listed in Table I below. TABLE 1 Examples of thecompounds of the formula (I) (I)

Ex. (position) (position) (position No. A R¹ R² (R³)n OAR⁴) R⁴ Physicaldata 3 CH₂

(2) Cl (4) Cl

logP = 2.04^(a)) 4 CH₂CH₂

(2) Cl (4) Cl

logP = 1.92^(a)) 5 CH₂CH₂

(2) Cl (4) Cl

logP = 1.52^(a)) 6 CH₂CH₂

(2) CH₃ (4) Cl

logP = 1.93^(a)) 7 CH₂CH₂

(2) CH₃ (4) Cl

logP = 1.68^(a)) 8 CH₂CH₂

(2) Cl (4) SCH₃

logP = 1.94^(a)) 9 CH₂CH₂

(2) Cl (4) SCH₃

logP = 1.58^(a)) 10 CH₂CH₂

(2) CH₃ (4) SCH₃

logP = 1.91^(a)) 11 CH₂CH₂

(2) Cl (4) SO₂CH₃

logP = 1.65^(a)) 12 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.07^(a)) 13 CH₂

(2) Cl (4) Cl

logP = 2.44^(a)) 14 CH₂CH₂

(2) Cl (4) SCH₃

logP = 2.05^(a)) 15 CH₂CH₂

(2) Cl (4) Cl

logP = 1.69^(a)) 16 CH₂CH₂

(2) Cl (4) Cl

logP = 1.92^(a)) 17 CH₂CH₂

(2) Cl (4) Cl

logP = 1.93^(a)) 18 CH₂CH₂

(2) Cl (4) Cl

logP = 1.62^(a)) 19 CH₂CH₂

(2) Cl (4) Cl

logP = 206^(a)) 20 CH₂

(2) Cl (4) SCH₃

(S enantiomer logP = 1.60^(a)) 21 CH₂CH₂

(2) Cl (4) Cl

logP = 2.39^(a)) 22 CH₂CH₂

(2) Cl (4) Cl

logP = 2.16^(a)) 23 CH₂CH₂

(2) Cl (4) Cl

logP = 2.40^(a)) 24 CH₂

(2) Cl (4) SCH₃

(S enantiomer) logP = 1.98^(a)) 25 CH₂CH₂

(2) CH₃ (4) Cl

logP = 1.88^(a)) 26 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.15^(a)) 27 CH₂CH₂

(2) Cl (4) Cl

logP = 2.11^(a)) 28 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.38^(a)) 29 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.12^(a)) 30 CH₂CH₂

(2) CH₃ (4) Cl

logP = 1.78^(a)) 31 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.38^(a)) 32 CH₂CH₂

(2) CH₃ (4) Cl

logP = 2.04^(a)) 33 CH₂CH₂

(2) Cl (4) SCH₃

logP = 1.97^(a)) 34 CH₂CH₂

(2) Cl (4) SCH₃

logP = 2.36^(a)) 35 CH₂

(2) CH₃ (4) Cl

(S enantiomer) [α]_(D) ²⁰ = +2.3 logP = 1.67^(a)) 36 CH₂

(2) CH₃ (4) Cl

(S enantiomer) logP = 1.94^(a)) 37 CH₂

(2) CH₃ (4) Cl

(S enantiomer) logP = 1.85^(a)) 38 CH₂

(2) CH₃ (4) Cl

(S enantiomer) logP = 2.10^(a)) 39 CH₂

(2) Cl (4) Cl

(S enantiomer) logP = 2.12^(a)) 40 CH₂

(2) Cl (4) Cl

(S enantiomer) logP = 1.67^(a)) 41 CH₂

(4) Cl —

logP = 2.42^(a)) 42 CH₂

(4) Cl —

logP = 1.65^(a)) 43 CH₂CH₂

(2) Cl (4) SCH₃

44 CH₂CH₂

(2) Cl (4) SCH₃

logP = 2.05^(a)) 45 CH₂

(2) Cl (4) SCH₃

(S enantiomer) logP = 1.68^(a)) 46 CH₂

(2) Cl (4) SCH₃

(S enantiomer) logP = 2.13^(a)) 47 CH₂

(2) Cl (4) Cl

(S enantiomer) logP = 1.95^(a)) 48 CH₂

(2) Cl (4) Cl

(S enantiomer) logP = 1.51^(a)) 49 CH₂

(4) Cl —

logP = 1.92^(a)) 50 CH₂CH₂

(2) Br (4) Br

n_(D) ²⁰ = 1.5970 51 CH₂CH₂

(2) Cl (4) Br

n_(D) ²⁰ = 1.5825 52 CH₂CH₂

(2) Cl (4) Cl

n_(D) ²⁰ = 1.5790 53 CH₂CH₂

(2) Cl (4) SO₂CH₃

m.p.: 69° C. 54 CH₂CH₂

(2) Cl (4) SO₂CH₃

m.p.: 62° C. 55 CH₂

(4) CF₃ —

56 CH₂

(4) CF₃ —

57 CH₂

(4) CF₃ —

58 CH₂

(4) CF₃ —

59 CH₂

(2) Br (4) Br

(S enantiomer) 60 CH₂

(2) Br (4) Br

(S enantiomer) logP = 1.56^(a)) 61 CH₂

(2) Br (4) Br

(S enantiomer) logP = 2.02^(a))

[0193] The log P values given in Table I were determined in accordancewith EEC Directive 79/831 V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18). Temperature: 43° C.

[0194] (a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient of 10%acetonitrile to 90% acetonitrile—the corresponding data in Table 1 arelabelled ^(a)).

[0195] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile, lineargradient from 10% acetonitrile to 90% acetonitrile—the correspondingdata in Table 1 are labelled ^(b)).

[0196] Calibration was carried out using unbranched alkan-2-ones (with 3to 16 carbon atoms) whose log P values are known (determination of thelog P values by the retention times using linear interpolation betweentwo successive alkanones).

[0197] The lambda-max values were determined in the maxima of thechromatographic signals using UV spectra from 200 nm to 400 nm.

[0198] Starting Materials of the Formula (II):

Example (II-1)

[0199]

[0200] Over a period of 4 to 6 hours, 43 g (0.606 mol) of chlorine gasare introduced into a boiling solution of 100 g (0.6 mol) of methyl3-hydroxy-2-methyl-benzoate and 0.4 ml of diisopropylamine in 800 ml of1,2-dichloro-ethane. After cooling, the solution is washed successivelywith in each case 200 ml of 5% strength sodium hydrogen sulphitesolution and with saturated sodium chloride solution, the organic phaseis dried over magnesium sulphate and the solvent is removed under waterpump vacuum. The dark-brown oil obtained as the residue is admixed with30 ml of diethyl ether and cooled to from 0° to 4° C. forcrystallization. The precipitated crystals are isolated by filtrationwith suction, washed with a little cold diethyl ether and dried underreduced pressure at 30° C.

[0201] This gives 46.6 g (39% of theory) of methyl4-chloro-3-hydroxy-2-methylbenzoate.

[0202] Log P: 2.14.

[0203] Using, instead of methyl 3-hydroxy-2-methyl-benzoate, thecorresponding ethyl ester, ethyl 4-chloro-3-hydroxy-2-methyl-benzoate isobtained by the same process.

[0204] Melting point: 51° C.

[0205] Step 2

[0206] A solution of 25 g (0.125 mol) of methyl4-chloro-3-hydroxy-2-methyl-benzoate in 400 ml of acetonitnile isadmixed successively with 34.2 g (0.248 mol) of powdered anhydrouspotassium carbonate and 29.3 g (0.125 mol) of 2-chloro-ethanol-p-toluenesulphonate. The reaction mixture is heated at 70° C. for about 7 hoursand then allowed to cool, and the major part of the solvent is removedunder water pump vacuum. The residue is dissolved in 200 ml ofdichloromethane and 300 ml of water. The organic phase is separated off,washed with water, dried over magnesium sulphate and filtered. From thefiltrate, the solvent is carefully distilled off under reduced pressure.

[0207] This gives 32.5 g (99% of theory) of methyl4-chloro-3-(2-chloro-ethoxy)-2-methylbenzoate as a dark oil.

[0208] Log P=3.52.

[0209] Step 3

[0210] A solution of 16.0 g (60.8 mmol) of methyl4-chloro-3-(2-chloro-ethoxy)-2-methylbenzoate in 70 ml of dimethylsulphoxide is admixed successively with 18.4 g (0.133 mol) of powderedanhydrous potassium carbonate and 6.9 g (60.8 mmol) of3,4-dimethyl-1,2,4-triazolin-5-one. The reaction mixture is heated at90° C., for about 6 hours and then allowed to cool, and the major partof the solvent is removed under water pump vacuum. The residue isdissolved in 140 ml of dichloromethane and 60 ml of water. The organicphase is separated off, washed with water, dried over magnesium sulphateand concentrated under water pump vacuum. The oily residue is stirredwith 25 ml of petroleum ether. The resulting crystalline product isisolated by filtration with suction.

[0211] This gives 18.5 g (80% of theory) of methyl4-chloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-benzoate.

[0212] Log P: 1.94.

Example (II-2)

[0213]

[0214] With ice-cooling, 3.3 g (44.5 mmol) of sodium methyl mercaptideare added to a solution of 12.4 g (36.5 mmol) of methyl4-chloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5‘-on-i’-yl)-ethoxy]-2-methyl-benzoatein 100 ml of N,N-dimethyl-formamide. The mixture is stirred at roomtemperature (about 20° C.) for about 6 hours, and the major part of thesolvent is removed under water pump vacuum. The residue is dissolved in300 ml of ethyl acetate and 200 ml of water. The organic phase isseparated off, washed with water, dried over magnesium sulphate andfiltered. From the filtrate, the solvent is carefully distilled offunder reduced pressure.

[0215] This gives 5.4 g (42% of theory) of methyl3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5‘-on-’-yl)-ethoxy]-2-methyl-4-methylthio-benzoate.

[0216] LogP=1.89.

Example (II-3)

[0217]

[0218] 10 mg of ammonium molybdate tetrahydrate and 17.3 g (178 mmol) ofa 35% strength aqueous hydrogen peroxide solution are added to asolution of 12.3 g (33.7 mmol) of ethyl3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-4-methylthio-benzoatein 40 ml of acetic acid. The reaction mixture is heated at from 50° to60° C. for about 6 hours, diluted with water and extracted with ethylacetate. The organic phase is separated off, washed successively withwater, sodium bicarbonate solution, sodium thiosulphate solution andagain with water, dried over magnesium sulphate and filtered. From thefiltrate, the solvent is carefully distilled off under reduced pressure.

[0219] This gives 12.3 g (92% of theory) of ethyl3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-4-methylsulphonyl-benzoate.

[0220] LogP=1.76.

Example (II-4)

[0221]

[0222] 1.2 g (30 mmol) of a solution of sodium hydroxide in 20 ml ofwater are added to a solution of 6.5 g (19.0 mmol) of methyl4-chloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-benzoatein 40 ml of ethanol. The solution is stirred at room temperature (about20° C.) for about 24 hours, and the major part of the solvent is removedunder water pump vacuum. The residue is dissolved in water and acidifiedwith hydrochloric acid. The resulting suspension is extracted with ethylacetate and the organic phase is separated off, washed with saturatedsodium chloride solution, dried over magnesium sulphate and filtered.From the filtrate the solvent is carefully distilled off under reducedpressure.

[0223] This gives 5.9 g (95% of theory) of4-chloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-methyl-benzoicacid.

[0224] Log P=1.37.

Example (II-5)

[0225]

[0226] 2.3 g (6.65 mmol) of2,4-dichloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-benzoicacid in 10 ml of thionyl chloride are heated at 70° C. for about 1.5hours. The reaction solution is allowed to cool and the excess thionylchloride is removed under reduced pressure.

[0227] This gives 2.4 g (100% of theory) of2,4-dichloro-3-[2-(3′,4′-dimethyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-ethoxy]-2-benzoylchloride.

[0228] Log P=1.24.

Example (II-6)

[0229]

[0230] 5 g (21.3 mmol) of ethyl 2,4-dichloro-3-hydroxy-benzoate aredissolved in 200 ml of tetrahydrofuran and admixed with 3.68 g (21.3mmol) of 1-hydroxymethyl-3-ethoxy-4-methyl-1,2,4-triazolin-5-one. 5.58 g(21.3 mmol) of triphenylphosphine are added, and at 0° C., 4.4 g of 85%diethyl diazo-dicarboxylate are then added dropwise. The resultingsolution is stirred overnight, concentrated under water pump vacuum andfiltered through silica gel (ethyl acetate/hexane). The filtrate isconcentrated and mixed with diethyl ether. The solid that separates offis filtered off, and the solvent is carefully distilled off from thefiltrate under reduced pressure.

[0231] This gives 6.8 g (82% of theory) of ethyl3-(3′-ethoxy-4′-methyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-methoxy-2,4-dichloro-benzoateas a viscous oil.

[0232] Log P=2.77.

Example (II-7)

[0233]

[0234] 2 g (8.5 mmol) of ethyl 2,4-dichloro-3-hydroxy-benzoate aredissolved in 30 ml of acetonitrile and mixed successively with 0.86 g(8.5 mmol) of triethylamine and 1.2 g (8.5 mmol) ofN-chloromethyl-2-pyridone. The resulting mixture is stirred at 60° C.for 7 hours, admixed with water and extracted with ethyl acetate. Theorganic phase is separated off, washed with saturated sodium chloridesolution, dried over magnesium sulphate and filtered. The solvent iscarefully distilled off under reduced pressure.

[0235] This gives 2.4 g (82% of theory) of ethyl2,4-dichloro-3-(1H-pyrid-2-on-1-yl)-methoxy-benzoate.

Example (II-8)

[0236]

[0237] 6.4 g (16.3 mmol) of ethyl3-(3′-ethoxy-4′-methyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-methoxy-2,4-dichloro-benzoateare stirred in a mixture of 250 ml of cyclohexane and 25 ml of ethyleneglycol monomethyl ether in the presence of 0.91 g of powdered potassiumhydroxide at room temperature (about 20° C.) for 15 hours. The mixtureis diluted with water and acidified with 2N hydrochloric acid. Theprecipitated solid is isolated by filtration with suction.

[0238] This gives 4.05 g (69% of theory) of3-(3′-ethoxy-4′-methyl-1′,2′,4′-1H-triazolin-5′-on-1′-yl)-methoxy-2,4-dichloro-benzoicacid.

[0239] log P: 1.74.

[0240] Analogously to Examples (II-1) to (II-8), it is also possible toprepare, for example, the compounds of the general formula (a,) listedin Table 2 below, or reactive derivatives thereof—cf. formula (IIA),

[0241] where

[0242] R has one of the meanings listed in the Table below. TABLE 2Examples of compounds of the formula (II) or (IIA) (position) (position)(position Ex. No. A R² (R³)_(n) OAR⁴) R⁴ R Physical data II-9  CH₂CH₂(2) CH₃ (4) Cl

C₂H₅ logP = 2.25^(a)) II-10 CH₂CH₂ (2) CH₃ (4) SCH₃

C₂H₅ logP = 2.16^(a)) II-11 CH₂CH₂ (2) CH₃ (4) SO₂CH₃

CH₃ logP = 1.48^(a)) II-12 CH₂CH₂ (2) CH₃ (4) SCH₃

H logP = 1.33^(a)) II-13 CH₂CH₂ (2) CH₃ (4) SO₂CH₃

H logP = 0.92^(a)) II-14 CH₂CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.08^(a)) II-15 CH₂CH₂ (2) Cl (4) Cl

H logP = 1.23^(a)) II-16 CH₂CH₂ (2) SCH₃ (4) SCH₃

C₂H₅ logP = 2.13^(a)) II-17 CH₂CH₂ (2) Cl (4) SCH₃

C₂H₅ logP = 2.09^(a)) II-18 CH₂CH₂ (2) Cl (4) SCH₃

H logP = 1.27^(a)) II-19 CH₂CH₂ (2) Cl (4) SOCH₃

H logP = 0.59^(a)) II-20 CH₂CH₂ (2) Cl (4) SO₂CH₃

C₂H₅ logP = 1.72^(a)) II-21 CH₂CH₂ (2) Cl (4) SO₂CH₃

H logP = 0.77^(a)) II-22 CH₂CH₂ (2) SO₂CH₃ (4) SO₂CH₃

H logP = 0.46^(a)) II-23 CH₂CH₂ (2) Cl (4) SOCH₃

C₂H₅ logP = 1.49^(a)) II-24 CH₂CH₂ (2) CH₃ (4) SO₂CH₃

H (xHCl) logP = 0.95^(a)) II-25 CH₂CH₂ (2) Cl (4) SO₂CH₃

H (xHCl) logP = 0.83^(a)) II-26 CH₂CH₂ (2) CH₃ (4) SCH₃

H (xHCl) logP = 1.34^(a)) II-27 CH₂CH₂ (2) Cl (4) SCH₃

H (xHCl) logP = 1.27^(a)) II-28 CH₂CH₂ (2) CH₃ (4) Cl

H (xHCl) logP = 1.37^(a)) II-29 CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.69^(a)) II-30 CH₂ (2) CH₃ (4) Cl

CH₃ logP = 2.13^(a)) II-31 CH₂ (2) Cl (4) Cl

H logP = 1.68^(a)) II-32 CH₂ (2) Cl (4) Cl

H ¹H-NMR (DMSO-D6). δ): 5.89 ppm (s, CH₂) II-33 CH₂CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.40^(a)) II-34 CH₂CH₂ (2) Cl (4) Cl

H logP = 1.52^(a)) II-35 CH₂CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.66^(a)) II-36 CH₂CH₂ (2) Cl (4) Cl

H logP = 1.72^(a)) II-37 CH₂CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.68^(a)) II-38 CH₂CH₂ (2) Cl (4) Cl

H logP = 1.73^(a)) II-39 CH₂CH₂ (2) Cl (4) Cl

C₂H₅ logP = 2.28^(a)) II-40 CH₂CH₂ (2) Cl (4) Cl

H logP = 1.45^(a)) II-41 CH₂CH₂ (2) CH₃ (4) Cl

CH₃ logP = 2.17^(a)) II-42 CH₂CH₂ (2) CH₃ (4) Cl

H logP = 1.78^(a)) II-43 CH₂CH₂ (2) CH₃ (4) Cl

CH₃ logP = 2.44^(a)) II-44 CH₂CH₂ (2) CH₃ (4) Cl

H logP = 1.75^(a)) II-45 CH₂CH₂ (2) CH₃ (4) Cl

CH₃ logP = 2.46^(a)) II-46 CH₂CH₂ (2) CH₃ (4) Cl

H logP = 1.79^(a)) II-47 CH₂CH₂ (2) CH₃ (4) Cl

CH₃ logP = 2.06^(a)) II-48 CH₂CH₂ (2) CH₃ (4) Cl

H logP = 1.49^(a)) II-49 CH₂CH₂ (2) Cl (4) SCH₃

C₂H₅ logP = 2.59^(a)) II-50 CH₂CH₂ (2) Cl (4) SCH₃

H logP = 1.64^(a)) II-51 CH₂CH₂ (2) Cl (4) SCH₃

C₂H₅ logP = 2.22^(a)) II-52 CH₂CH₂ (2) Cl (4) SCH₃

H logP = 1.37^(a)) II-53 CH₂ (2) Cl (4) SCH₃

C₂H₅ (S enantiomer) logP = 2.17^(a)) II-54 CH₂ (2) Cl (4) SCH₃

H (S enantiomer) logP = 1.31^(a)) II-55 CH₂ (2) Cl (4) SCH₃

C₂H₅ (S enantiomer) logP = 1.31^(a)) II-56 CH₂ (2) Cl (4) SCH₃

H (S enantiomer) logP = 1.44^(a)) II-57 CH₂ (2) CH₃ (4) Cl

C₂H₅ (S enantiomer) logP = 1.95^(a)) II-58 CH₂ (2) CH₃ (4) Cl

H (S enantiomer) logP = 1.39^(a)) II-59 CH₂ (2) CH₃ (4) Cl

C₂H₅ (S enantiomer) logP = 2.18^(a)) II-60 CH₂ (2) CH₃ (4) Cl

H (S enantiomer) logP = 1.55^(a)) II-61 CH₂ (2) Cl (4) Cl

C₂H₅ (S enantiomer) logP = 2.15^(a)) II-62 CH₂ (2) Cl (4) Cl

H (S enantiomer) logP = 1.28^(a)) II-63 CH₂ (2) Cl (4) Cl

C₂H₅ (S enantiomer) II-64 CH₂ (2) Cl (4) Cl

CH₃ (S enantiomer) n_(D) ²⁰ = −20.4 logP = 2.01^(a)) II-65 CH₂ (2) Cl(4) Cl

H (S enantiomer) logP = 1.42^(a)) II-66 CH₂ (4) Cl —

CH₃ logP = 2.33^(a)) II-67 CH₂ (4) Cl —

H logP = 1.81^(a)) II-68 CH₂ (4) Cl —

CH₃ logP = 2.23^(a)) II-69 CH₂ (4) Cl —

CH₃ logP = 2.07^(a)) II-70 CH₂ (4) Cl —

H logP = 1.36^(a)) II-71 CH₂ (4) CF₃ —

CH₃ II-72 CH₂ (4) CF₃ —

H II-73 CH₂ (4) CF₃ —

CH₃ II-74 CH₂ (4) CF₃ —

H II-75 CH₂ (2) Br (4) Br

C₂H₅ (S enantiomer) logP = 2.20^(a)) II-76 CH₂ (2) Br (4) Br

C₂H₅ (S enantiomer) logP = 2.46^(a)) II-77 CH₂ (2) Br (4) Br

H (S enantiomer) logP = 1.34^(a)) II-78 CH₂ (2) Br (4) Br

H (S enantiomer) logP = 1.49^(a))

[0243] The compound listed in Table 2 as Example (II-35) can beprepared, for example, as follows:

Example (II-35)

[0244] Step 1

[0245] A solution of 15 g (68 mmol) of ethyl2,4-dichloro-3-hydroxy-benzoate in 80 ml of N,N-dimethyl-formamide isadmixed successively with 19 g (137 mmol) of potassium carbonate(powder), 38.6 g (205 mmol) of 1,2-dibromo-ethane and 0.4 g of sodiumiodide. The mixture is heated at 80° C. for 2 hours and then allowed tocool to room temperature and shaken with 350 ml of diethyl ether. Theorganic phase is washed with water, 10% strength aqueous sodiumhydroxide solution and finally with 10% strength hydrochloric acid andthen dried with sodium sulphate and filtered. From the filtrate, thesolvent is carefully distilled off under reduced pressure.

[0246] This gives 22.2 g (95% of theory) of ethyl2,4-dichloro-3-(2-bromo-ethoxy)-benzoate as an oily residue (logP=3.98^(a)))

[0247] Step 2

[0248] A solution of 18 g (93 mmol) of ethyl2,4-dichloro-3-(2-bromo-ethoxy)-benzoate in 100 ml ofN,N-dimethyl-formamide is admixed successively with 14.6 g (106 mmol) ofpotassium carbonate (powder), 19.3 g (133 mmol) of3-methylthio-4-methyl-1,2,4-triazolin-5-one and 0.5 g of sodium iodide.The mixture is heated at 80° C. for 4 hours and then cooled to roomtemperature and shaken with 400 ml of dichloromethane, and the organicphase is washed with water, then with 10% strength aqueous sodiumhydroxide solution and finally with 10% strength hydrochloric acid, thendried with sodium sulphate and filtered. From the filtrate, the solventis carefully distilled off under reduced pressure.

[0249] This gives 17.7 g (82% of theory) of ethyl2,4-dichloro-3-[2-(3-methylthio-4-methyl-5-oxo-1,2,4-triazolin-1-yl)-ethoxy]-benzoateas an oily residue (logP=2,66 ^(a))).

[0250] The compound listed in Table 2 as Example (II-61) can beprepared, for example, as follows:

Example (II-61)

[0251]

[0252] A mixture of 2.0 g (8.5 mmol) of ethyl2,4-dichloro-3-hydroxy-benzoate, 3.6 g (12.75 mmol) of(S)-(+)-5-(p-tolylsulphonyloxymethyl)-pyrrolidin-2-one, 2.3 g (17 mmol)of potassium carbonate and 30 ml of acetonitrile is stirred at 76° C.for 13 hours, cooled to room temperature, diluted with water to abouttwice its original volume and shaken with methylene chloride. Theorganic phase is washed with saturated aqueous sodium chloride solution,dried with sodium sulphate and filtered. From the filtrate, the solventis carefully distilled off under reduced pressure.

[0253] This gives 2.6 g (92% of theory) of ethyl(S)-2,4-dichloro-3-[(2-oxo-pyrrolidin-5-yl)-methoxy]-benzoate (logP=2.14^(a))).

[0254] Use Examples:

Example A

[0255] Pre-emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0256] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0257] Seeds of the test plants are sown in normal soil. After 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of active compound in the spray liquor is chosensuch that the particular amount of active compound desired is applied in1000 liters of water per hectare. After three weeks, the degree ofdamage to the plants is rated in % damage in comparison to thedevelopment of the untreated control. The figures denote:

[0258] 0%=no effect (like untreated control)

[0259] 100%=total destruction

[0260] In this test, for example, the compounds of Preparation Examples1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 11 show strong activity against weeds,and most of them are tolerated well by crop plants, such as, forexample, maize.

Example B

[0261] Post-emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0262] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0263] Test plants with a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen so that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

[0264] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0265] The figures denote:

[0266] 0%=no effect (like untreated control)

[0267] 100%=total destruction

[0268] In this test, for example, the compounds of Preparation Examples1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 13 show strong activity againstweeds, and some are tolerated well by crop plants, such as for example,maize.

1. Substituted aryl ketones of the general formula (I)

in which n represents the number 0, 1 or 2, A represents alkanediyl(alkylene), R¹ represents one of the groupings below

where m represents the numbers 0 to 6, R⁵ represents halogen orrepresents in each case optionally substituted alkyl, alkylthio or arylor—if m represents 2—optionally also together with a second radical R⁵represents alkanediyl (alkylene), R⁶ represents hydroxyl, formyloxy,halogen, or represents in each case optionally substituted alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy,alkinyloxy, aryloxy, arylthio, arylsulphinyl, arylsulphonyl,arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy,arylalkylthio, arylalkylsulphinyl or arylalkylsulphonyl, R⁷ representshydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents ineach case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkoxycartonyl or cycloalkyl, R⁸represents hydrogen or represents in each case optionally substitutedalkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,R⁹ represents hydroxyl, formyloxy, or represents in each case optionallysubstituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy, R¹⁰represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, R¹¹represents hydrogen or represents in each case optionally substitutedalkyl or cycloalkyl, R¹² represents hydrogen or represents in each caseoptionally substituted alkyl or cycloalkyl, and R¹³ represents hydrogen,cyano, carbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl oralkylsulphonyl, R² represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl, R³ represents nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents ineach case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl, and R⁴ represents an optionally substituted 4- to12-membered, saturated or unsaturated, monocyclic or bicyclicheterocyclic grouping which contains 1 to 4 hetero atoms (up to 4nitrogen atoms and optionally—alternatively, or additionally—one or twooxygen atoms or one or two sulphur atoms, or one or two SO groupings orone or two SO₂ groupings), and which additionally contains one to threeoxo groups (C═O) and/or thioxo groups (C═S) as components of theheterocycle, —including all possible tautomeric forms of the compoundsof the general formula (I) and the possible salts and acid or baseadducts of the compounds of the general formula (I)—.
 2. Compounds ofthe formula (I) according to claim 1, characterized in that n representsthe number 0 or 1, m represents the number 0, 1, 2, 3 or 4, A representsalkanediyl (alkylene) having 1 to 6 carbon atoms, R¹ represents one ofthe groupings below

R² represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, R³ represents nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, R⁴ represents one of the heterocyclic groupings below

where in each case the broken bond is a single bond or a double bond, Qrepresents oxygen or sulphur, R¹⁴ represents hydrogen, hydroxyl,mercapto, cyano, halogen, represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-thio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms in the alkyl groups, represents in eachcase optionally halogen-substituted alkylamino or dialkylamino having ineach case up to 6 carbon atoms in the alkyl groups, represents in eachcase optionally halogen-substituted alkenyl, alkinyl, alkenyloxy,alkenylthio or alkenylamino having in each case up to 6 carbon atoms inthe alkenyl or alkinyl cycloalkyl, cycloalkyloxy, cycloalkylthio,cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthioor cycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally up to 4 carbon atoms in the alkylmoiety, or represents in each case optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino,piperidino or morpholino, or—if two adjacent radicals R¹⁴ and R¹⁴ arelocated at a double bond—also together with the adjacent radical R¹⁴represents a benzo grouping, and R¹⁵ represents hydrogen, hydroxyl,amino, alkylideneamino having up to 4 carbon atoms, represents in eachcase optionally halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy,alkylamino, dialkylamino or alkaneoylamino having in each case up to 6carbon atoms in the alkyl groups, represents in each case optionallyhalogen-substituted alkenyl, alkinyl or alkenyloxy having in each caseup to 6 carbon atoms in the alkenyl or alkinyl groups, represents ineach case optionally halogen-substituted cycloalkyl, cycloalkylalkyl orcycloalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally up to 3 carbon atoms in the alkylmoiety, or represents in each case optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted phenyl or benzyl, or together with an adjacentradical R¹⁴ or R¹⁵ represents optionally halogen- orC₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,  wherethe individual radicals R¹⁴ and R¹⁵ —if more than one of them areattached to the same heterocyclic groupings—can have identical ordifferent meanings within the scope of the above definition, R⁵represents halogen, represents in each case optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl or alkylthio having in each case 1 to6 carbon atoms, represents optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted phenyl, or optionally also—if m represents2—together with a second radical R⁵ represents alkanediyl having 2 to 6carbon atoms, R⁶ represents hydroxyl, formyloxy, or represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy,alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulphonyloxy having ineach case 1 to 6 carbon atoms in the alkyl groups, represents in eachcase optionally cyano- or halogen-substituted alkenyloxy or alkinyloxyhaving in each case 2 to 6 carbon atoms, or represents in each caseoptionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted aryloxy, arylthio,arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy,arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl orarylalkylsulphonyl having in each case 6 or 10 carbon atoms in the arylgroup and optionally 1 to 4 carbon atoms in the alkyl moiety, R⁷represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atomsin the alkyl groups, or represents optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R⁸represents hydrogen, represents in each case optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms, representsin each case optionally cyano- or halogen-substituted alkenyl or alkinylhaving in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atomsin the alkyl moiety, R⁹ represents hydroxyl, formyloxy, represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy substitutedalkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, orrepresents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted arylalkoxy, arylcarbonyloxy,arylcarbonylalkoxy or arylsulphonyloxy having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, R¹⁰ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl,alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6carbon atoms in the alkyl groups, R¹⁰ represents hydrogen, representsoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1to 6 carbon atoms or represents optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R¹²represents hydrogen, represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms or representsoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having3 to 6 carbon atoms, and R¹³ represents hydrogen, cyano, carbamoyl,halogen, or represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl groups.
 3. Compounds of the formula (I) according to claim1 or 2, characterized in that m represents the numbers 0, 1, 2 or 3, Arepresents methylene, ethane-1,2-diyl (dimethylene), ethane-1,1-diyl,propane-1,2-diyl, propane-1,3-diyl (trimethylene), butane-1,2-diyl, R²represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,fluorine, chlorine, bromine, iodine, or represents in each caseoptionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine- and/or chlorine-,methoxy- ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or representsmethylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, R³represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, represents in each case optionally fluorine- and/orchlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine- and/orchlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,ethoxy, n- or i-propoxy, represents in each case optionally fluorine-and/or chorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or representsmethylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, R⁴represents one of the heterocyclic groupings below,

R⁵ represents fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, representsoptionally fluorine-, chlorine-, methyl- or methoxy-substituted phenyl,or optionally also—if m represents 2—together with a second radical R⁵represents ethane-1,2-diyl (dimethylene), propane-1,3-diyl(trimethylene) or butane-1,4-diyl (tetramethylene), R⁶ representshydroxyl, formyloxy, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n-or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, acetyloxy, propionyloxy, n- ori-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n-or i-propylsulphonyloxy, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,propinyloxy or butinyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenoxy, phenylthio, phenylsulphinyl,phenylsulphonyl, benzoyloxy, benzoylmethoxy, phenylsulphonyloxy,phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl orphenylmethylsulphonyl, R⁷ represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R⁸represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl or benzyl, R⁹represents hydroxyl, formyloxy, represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,propinyloxy or butinyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenylmethoxy, benzoyloxy, benzoylmethoxyor phenylsulphonyloxy, R¹⁰ represents hydrogne, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-,s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, R¹¹ represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, R¹² represents hydrogen, represents in eachcase optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, R¹³ represents hydrogen, cyano, carbamoyl,fluorine, chlorine, bromine, or represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, R¹⁴ represents hydrogen,hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine,represents in each case optionally fluorine-, chlorine-, methoxy-,ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-,ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substitutedmethyl, ethyl, n- , s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or 1-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino,represents in each case optionally fluorine- and/or chlorine-substitutedethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy,butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino,represents in each case optionally fluorine- and/or chlorine-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio,cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino,cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino,or represents in each case optionally fluorine-, chlorine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n-or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino,piperidino or morpholino, or—if two adjacent radicals R¹⁴ and R¹⁴ arelocated at a double bond—together with the adjacent radical R¹⁴ alsorepresents a benzo grouping, and R¹⁵ represents hydrogen, hydroxyl,amino, represents in each case optionally fluorine- and/or chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- ors-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino ordimethylamino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, ethinyl, propinyl orpropenyloxy, represents in each case optionally fluorine- and/orchlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, or represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i- s- or t-butyl-,methoxy-, ethoxy-, n- or -propoxy-substituted phenyl or benzyl, ortogether with an adjacent radical R¹⁴ or R¹⁵ represents in each caseoptionally methyl- and/or ethyl-substituted propane-1,3-diyl(trimethylene) or butane-1,4-diyl (tetramethylene).
 4. Compounds of theformula (I) according to any of claims 1 to 3, characterized in that mrepresents the number 0, 1 or 2, A represents methylene or dimethylene,R² represents hydrogen, nitro, cyano, fluorine, chlorine, bromine,iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, R³ represents nitro, cyano, fluorine, chlorine,bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl,dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl,methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, R⁵ represents in each case optionally fluorine-or chlorine-substituted methyl, ethyl, n- or i-propyl, methylthio,ethylthio, n- or i-propylthio, represents phenyl, or optionally also—ifm represents 2—together with a second radical R⁵ representsethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene) orbutane-1,4-diyl (tetramethylene), R⁶ represents hydroxyl, formyloxy,represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylpropionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents propenyloxy or propinyloxy, orrepresents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-,ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenoxy, phenylthio, phenylsulphinyl,phenylsulphonyl, benzoyloxy, benzoylmethoxy, phenylsulphonyloxy,phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl orphenylmethylsulphonyl, R⁷ represents hydrogen, cyano, fluorine,chlorine, bromine, represents in each case optionally fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, R⁸ representshydrogen, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,represents in each case optionally fluorine- or chlorine-substitutedpropenyl or propinyl, represents optionally fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, or represents ineach case optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl or benzyl, R⁹represents hydroxyl, formyloxy, represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propyldulphonylocy,represents propenyloxy or propinyloxy, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenylmethoxy, benzoyloxy, benzoylmethoxy or phenylsulphonyloxy, R¹⁰represents hydrogen, cyano, fluorine, chlorine, bromine, or representsin each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl,n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, R¹¹ represents hydrogen, represents in each caseoptionally fluorine-, chlorine-, bromine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, R¹² represents hydrogen, represents ineach case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, R¹³ represents hydrogen, cyano, fluorine,chlorine, bromine, or represents in each case optionally fluorine-,chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- ori-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, R¹⁴ representshydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine,iodine, represents in each case optionally fluorine-, chlorine-,methoxy-, ethoxy-, n- or 1-propoxy-, methylthio-, ethylthio-, n- orsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, representsmethylamino, ethylamino, n- or i-propylamino, dimethylamino ordiethylamino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, ethinyl, propinyl, propenyloxy,propenylthio or propenylamino, represents in each case optionallyfluorine- and/or chlorine-substituted cyclopropyl, cyclopropyloxy,cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy orcyclopropylmethylamino, or represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- ori-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, or - if two adjacentradicals R¹⁴ and R¹⁴ are located at a double bond—together with theadjacent radical R¹⁴ also represents a benzo grouping, and R¹⁵represents hydrogen, hydroxyl, amino, represents in each case optionallyfluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino,ethylamino or dimethylamino, represents propenyl or propinyl, representsin each case optionally fluorine- and/or chlorine-substitutedcyclopropyl, cyclobutyl or cyclopropylmethyl, or represents in each caseoptionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-,methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, ortogether with an adjacent radical R¹⁴ or R¹⁵ represents in each caseoptionally methyl- and/or ethyl-substituted propane-1,3-diyl(trimethylene) or butane-1,4-diyl (tetramethylene).
 5. Process forpreparing compounds of the formula (I) according to any of claims 1 to4, characterized in that (a) substituted benzoic acids of the generalformula (II)

 in which n, A, R², R³ and R⁴ are each as defined in claim 1, orreactive derivatives thereof, such as, for example, the correspondingacid halides, acid cyanides or esters—  are reacted with compounds ofthe general formula (m[[) R¹—H  (III)  in which R¹ is as defined inclaim 1, if appropriate in the presence of a dehydrating agent, ifappropriate in the presence of one or more reaction auxiliaries and ifappropriate in the presence of a diluent,  or in that (b) substitutedbenzoyl ketones of the general formula (Ia)

 in which n, A, R², R³, R⁴ and R¹¹ are each as defined in claim 1, arereacted with an orthoformic ester or a N,N-dimethyl-formamide acetal orand then with hydroxylamine or an acid adduct thereof, if appropriate inthe presence of one or more reaction auxiliaries and if appropriate inthe presence of one or more diluents, and, if appropriate, following thepractice of the process (a) or (b) according to the invention, theresulting compounds of the general formula (I) are subjected in acustomary manner to substitution, oxidation or reduction reactionswithin the scope of the definition of the substituents and/or thecompounds of the general formula (I) are converted in a customary mannerinto salt-like compounds.
 6. Compounds of the formula (II)

in which n, A, R², R³ and R⁴ are each as defined in claim 1, andreactive derivatives thereof.
 7. Process for preparing compounds of theformula (II) according to claim 6, characterized in that (α) Compoundsof the formula (IV)

 in which n, A, R² and R³ are each as defined in claim 1 and X¹represents halogen or represents alkylsulphonyloxy  or else derivativesthereof—  are reacted with heterocyclic compounds of the general formula(V) H—R⁴  (V)  in which R⁴ is as defined in claim 1, if appropriate inthe presence of an acid acceptor and if appropriate in the presence of adiluent, at temperatures between 10° C. and 150° C., followed, ifappropriate, by further customary conversion reactions within the scopeof the definition of the substituents,  or in that (β) compounds of theformula (VI)

10 in which n, R² and R³ are each as defined in claim 1, or elsederivatives thereof—  are reacted with hydroxyalkylheterocycles of thegeneral formula (VII)

 in which A and R⁴ are each as defined in claim 1, in the presence ofcondensing agents and, if appropriate, in the presence of a diluent, attemperatures between −20° C. and +50° C., followed, if appropriate, byfurther customary conversion reactions within the scope of thedefinition of the substituents, or in that (γ) compounds of the formula(VI)

 in which n, R2 and R3 are each as defined in claim 1, or elsederivatives thereof—  are reacted with halogenoalkylheterocycles of thegeneral formula (VIII)

 in which A and R⁴ are each as defined in claim 1 and X² representshalogen, represents alkylsulphonyloxy or represents if appropriate inthe presence of an acid acceptor and if appropriate in the presence of adiluent, at temperatures between 0° C. and 150° C., followed, ifappropriate, by further customary conversion reactions within the scopeof the definition of the substituents.
 8. Compounds of the formula (Ia)

in which n, A, R², R³, R⁴ and R¹¹ are each as defined in claim
 1. 9.Compositions, characterized in that they comprise at least one compoundof the formula (I) according to any of claims 1 to
 4. 10. Use ofcompounds of the formula (I) according to any of claims 1 to 4 or ofcompositions according to claim 9 for controlling undesirable plants.11. Method for controlling undesirable plants, characterized in that atleast one compound of the formula (I) according to any of claims 1 to 4or a composition according to claim 9 is allowed to act on undesirableplants and/or their habitats.